Dichloromethane → HCID 59424645, compound

HRID 1710916Notes

Reaction equation

HRID 1710916 reaction equation
C(OC(=O)[O:7][CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:26][C:25]3[C:20](=[N:21][CH:22]=[CH:23][C:24]=3[O:27][C:28]3[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38](=[O:46])[CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[S:36])=[CH:30][C:29]=3[F:47])[CH:19]=2)=[CH:14][CH:13]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[F:47][C:29]1[CH:30]=[C:31]([NH:34][C:35]([NH:37][C:38](=[O:46])[CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[S:36])[CH:32]=[CH:33][C:28]=1[O:27][C:24]1[CH:23]=[CH:22][N:21]=[C:20]2[CH:19]=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([CH2:11][NH:10][CH2:9][CH2:8][OH:7])=[CH:17][CH:16]=3)[S:26][C:25]=12

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59424595HCID 59424595, compound

Product 1

HCID 59424645HCID 59424645, compound

Procedure

To a solution of 62 in DCM (190 mg, 0.24 mmol) was added TFA (excess) at room temperature and the reaction mixture was stirred for 3 hrs, evaporated under reduced pressure and the residual solid was triturated with Et2O to afford the title compound 63 as the di-TFA salt (100 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.49 (s, 1H), 11.84 (s, 1H), 8.89 (s, 1H), 8.53 (d, J=5.1 Hz, 1H), 8.14 (s, 1H), 8.01 (m, 1H), 7.62 (dd, J=2.5 and 7.7 Hz, 2H), 7.54 (d, J=2.7 Hz, 2H), 7.33 (m, 4H), 7.28 (m, 1H), 6.67 (d, J=5.5 Hz, 1H), 4.64 (m, 1H), 4.30 (m, 1H), 4.22 (t, J=5.3 Hz, 2H), 3.82 (s, 2H), 3.63 (t, J=5.3 Hz, 2H), 2.98 (m, 1H). MS (m/z) 587.0 (M+H).

Workup

  1. customevaporated under reduced pressure
  2. customthe residual solid was triturated with Et2O

Sources & evidence

ORD record
ord-9bf0d6153421452d8b7334722f116ae8
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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